Dear Doris, Help! My Boyfriend Doesn’t Sail

My Boyfriend Doesn't Sail


By Clarity Nicoll

Photo credit: Offshore Sailing School. Contact at 800-221-4326 or;
CAPTIONS: In photo file names – a few other shots have been added witout caps yet – choose any and we will caption in the layout.

I grew up in a sailing family. My mother comes from a long line of sailors, my dad works in the marine industry and my brother and I have travelled up and down the eastern coast racing with and against each other. Yet, somehow, I had fallen in love with a No,ON-sailor (please note, the use of capital letters).

I had tried to introduce Dustin to sailing with some success, however, with the fast-paced nature of racing, and experienced sailors always ready to lend a hand when someone yelled “pull the cunningham!!!!”, he was having a hard time actually learning and becoming comfortable hopping on a boat.

Clarity on the Helm
Clarity’s turn on the helm was fun in 15-18 knots of breeze

Through my many sailing connections someone had mentioned Steve and Doris Colgate’s Offshore Sailing School. So, I wrote to Doris about my predicament and to my delight, she wrote back! “My Dear, I think the Fast Track to Cruising is what you need”.

So, I pitched the idea to Dustin. Fast Track to Cruising is a 7-day course in beautiful St. Petersburg, Florida where we would learn how to cruise together with the goal of being able to do our charter cruise vacation. I waited until after our flights were purchased to mention that there were 3 certification exams and a little bit of pre-vacation homework. He wasn’t amused.


Boat Briefing
Boat Briefing on the Catalina 40 with the pelicans before we head out on our cruising course






























Prior to the sailing course, it is highly recommended that you read the US Sailing Certification Series textbooks that the course is centered around: Basic Keelboat, Basic Cruising and Bareboat Cruising (the first two are available for online purchase through the US Sailing App). Steve and Doris also have a Fast Track to Cruising textbook that follows the flow of the course and consolidates most of the information. For a non-sailor, this pre-trip reading was essential as it prepares you for the entire course.

The Colgate Offshore Sailing School has six locations, four on the Gulf Coast of Florida and two in the British Virgin Islands. In St Petersburg, the sailing school has an affiliation with the Hampton Inn which is walking distance from the marina. We checked into the hotel on the Friday night after exploring beautiful St. Petersburg and got ready for the early morning in the classroom.

The first 2 days focuses on the Basic Keelboat course. With an 8am start time, we were in the classroom reviewing parts of the boat, manoeuvers, points of sail and practicing knots before heading to the marina to take a look at the Colgate 26, a great learn-to-sail keelboat designed by Steve Colgate and Jim Taylor.


The Art of Loading a Winch
Dustin learning the art of loading a winch on a Colgate 26

The next two days were spent loading winches, hoisting sails, gybing, tacking, reefing, the rules of sailing, and pretty much everything that was once gibberish to Dustin. We traded off being the skipper and being the crew on the boat. It was fast paced and intense, but it made us look forward to our free evenings. Since I had picked the vacation, Dustin was allowed to be captain of our evening plans. We are both foodies and generally organize our vacations around where we want to eat. St. Petersburg has some really incredible restaurants and fun bars that made for some exciting evenings. This included a visit to the St. Petersburg Ribfest complete with a performance by the Barenaked Ladies which made us Canadians feel right at home.

Dustin's Mastery
Dustin quickly mastered learning how to read a chart and plot a course

After we had passed our Basic Keelboat Certification, came the most anticipated part of the trip. We would be spending the next 5 days living aboard a Catalina 44 while completing our Basic Cruising and Bareboat Cruising course. Normally Dustin and I travel with matching London Fog roller suitcases but we packed up our waterproof Helly Hansen and Gill bags and walked over the boat to meet Hunter, our captain and instructor for rest of the week. Hunter had sailed his way to Florida after retiring in New York and he started his retirement gig teaching his way around the Florida Gulf Coast.

As always when taking off on a cruise, you start with provisioning. The Offshore School provides top notch provisioning with tons of options. I had to ask how many people were coming since the food took us 20 minutes to unload and put away, but I was assured that it would be just the three of us. Dustin and I, the foodies, were taking stock of the provisions while planning out some of the great meals that we would cook. I was really looking forward to learning how to use the appliances and electrical systems to be able to cook up a feast on any boat.

Hunter gave us the orientation and went through our pre-departure checklist which Dustin and I would then go through every morning before setting sail. This included checking the engine, bilge, electrical, the radio and our day plan. Hunter had already planned our trip but after meeting Dustin and me, and understanding our search for more local colour, we planned a new trip that would take us to some ports that would have some fun night life.

Dustin took the wheel and we headed for Golfport. The Catalina 44 was equipped with the latest electronics from Raymarine so Dustin used the chartplotter to set a course and we both learned about navigational marks on the Intracoastal Waterway. There were three bridges that we would have to go under so we had a lesson on how to determine bridge height during the different tide levels to make sure that our 64-foot mast would fit.

That first evening, we would be setting an anchor, so we reviewed the basics and put our skills to the test. After double checking that our anchor was placed properly and getting our dinghy ready, we poured a well-deserved glass of wine to enjoy while reviewing everything that we had learned that day. Later that evening, Dustin learned how to use the outboard engine on the dinghy and took us safely to shore so that we could explore some of the bars and restaurants. Golfport definitely provided some of the local colour that we were looking for.

The next morning we charted a course to Clearwater. By then we were pros with the anchor and the pre-departure checks. The learning experience was natural. Hunter would tell Dustin how cool paper charts were and he would grab the compass and slide ruler, plot where we were on the chart and get us a bearing to our destination. We had reserved a slip for overnight and I was mentally preparing to dock the 44-ft boat with no bow thrusters. Hunter showed me how to create engine wash to nail the docking.


Helming With Dustin
Helming was easier than Dustin thought with the help of the Offshore Sailing School instructor














After cooking up some steaks and potatoes on the barbeque, Hunter and I spent the evening reminiscing about charter vacations in the BVI’s. I had told Dustin all about my adventures exploring the baths, jumping off Willie T’s and having a Painkiller at the Soggy Dollar. The last few days made us really start to realize that chartering a boat in the BVIs might actually be a reality. This inspired our next adventure which was exploring Clearwater on the hunt for a Painkiller. We found one but it wasn’t the same. Dustin and I would have to get there with our new-found cruising skills and have a real Painkiller.

Dustin was a pro getting the boat off the dock the next morning as we sailed for Pinellas, the site of a beachside tikki bar. It was such a beautiful day that we just sailed the whole way. Dustin skippered while I marinated the shrimp for dinner. Hunter said that he had never eaten so well while on a course. I started to get the feeling that Dustin was beginning to like this whole sailing thing.

Once you do anchoring a couple of times it works like clockwork

The next morning, the weather started to turn. There was rain and 28 knots of breeze. We put our reefing skills to the test while I got to have a little fun driving the boat through some pretty big swells – now that it what I call a vacation! We saved the man overboard drills for the next day since we were afraid of losing the flotation device. But don’t worry, we both aced driving the boat while performing man overboard drills while under sail the next day.

Somewhere between us both learning to pick up mooring balls, learning to gas the boat and doing docking drills, we passed both of the remaining certification exams making our week a success. Dustin and I like to celebrate everything with a bottle of Veuve Cliquot, so while I prepped the Mahi Mahi for dinner, he picked up a bottle of bubbly to toast our success in now being ready to take on any sailing adventure together. We had one last adventure in St. Petersburg when we found a free concert before headed to St. Pete’s Beach to enjoy couple hours with our toes in the sand before heading to the airport.

Flying Colours
We passed our courses with flying colours and celebrated with Veuve Clicquot

The whole week was an incredible experience for us, Dustin gained confidence on the boat and I got to develop my chartering skills. For any other couples finding themselves in the same predicament, Steve and Doris Colgate’s Offshore Sailing School is a great place to start. Now, I don’t call Dustin my NON-sailing boyfriend – I am excited to I call him My Sailing Fiancé.

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